Carbon Tetrachloride → HCID 178526513, compound

HRID 710221Notes

Reaction equation

HRID 710221 reaction equation
[C:1]([C:5](O)=O)([F:4])([F:3])[F:2].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCN(CC)CC.[CH:34]1([C:37]2[CH:42]=[CH:41][C:40]([N+:43]([O-:45])=[O:44])=[CH:39][C:38]=2[NH2:46])[CH2:36][CH2:35]1.C(Cl)(Cl)(Cl)[Cl:48]>>[Cl:48]/[C:5](=[N:46]\[C:38]1[CH:39]=[C:40]([N+:43]([O-:45])=[O:44])[CH:41]=[CH:42][C:37]=1[CH:34]1[CH2:36][CH2:35]1)/[C:1]([F:4])([F:3])[F:2]

Participants

6

Reactant 5

HCID 5943Carbon TetrachlorideHCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 580658012-Cyclopropyl 5-nitrobenzenamine

Product 1

HCID 178526513HCID 178526513, compound

Procedure

A mixture of CF3CO2H (0.98 mL, 12.65 mmol, 0.9 eq), PPh3 (9.21 g, 35.13 mmol, 2.5 eq) and Et3N (1.96 mL, 14.05 mmol, 1.0 eq), in 25 mL CCl4 was stirred at 0° C. for 10 minutes. 2-Cyclopropyl-5-nitrobenzeneamine (2.50 g, 14.05 mmol, 1.0 eq) was then added to the reaction mixture and the mixture was heated to reflux for 12 hours. Solvent was removed under reduced pressure and the residue was purified by column chromatography, eluting with n-hexane: ethyl acetate (10:1), giving the (Z)—N-(1-chloro-2,2,2-trifluoroethylidene)-2-cyclopropyl-5-nitrobenzenamine intermediate in semi pure form as a light yellow solid. This compound was taken to the next step with out further purification.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 12 hours
  3. customSolvent was removed under reduced pressure
  4. customthe residue was purified by column chromatography
  5. washeluting with n-hexane: ethyl acetate (10:1)

Sources & evidence

ORD record
ord-6c56f8dcb16c4d60bd56a82361a88739
Source dataset
uspto-grants-2015_11
Patent number
US09181222B2

Reaction notes

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